#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/81/2208148.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208148
loop_
_publ_author_name
'S. Athimoolam'
'R. K. Rajaram'
_publ_section_title
;
 Thiaminium bis(bisulfate) monohydrate
;
_journal_coeditor_code           RZ6148
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o410
_journal_page_last               o413
_journal_paper_doi               10.1107/S1600536805041620
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H18 N4 O S 2+, 2H S O4 -, H2 O'
_chemical_formula_moiety         'C12 H18 N4 O S 2+, 2H S O4 -, H2 O'
_chemical_formula_sum            'C12 H22 N4 O10 S3'
_chemical_formula_weight         478.52
_chemical_name_common            'Thiaminium bis(bisulfate) monohydrate'
_chemical_name_systematic
;
Thiaminium bis(bisulfate) monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.83(4)
_cell_angle_beta                 82.67(6)
_cell_angle_gamma                83.23(5)
_cell_formula_units_Z            2
_cell_length_a                   7.686(3)
_cell_length_b                   10.801(7)
_cell_length_c                   12.881(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.24
_cell_measurement_theta_min      11.14
_cell_volume                     986.0(11)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL/PC and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  SHELXTL/PC
_computing_structure_solution    'SHELXTL/PC (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius MACH3 sealed-tube'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0095
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4297
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      1.601
_exptl_crystal_density_method
'flotation using a mixture of carbon tetrachloride and bromoform'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.583
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0485P)²+1.0125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                2898
_reflns_number_total             3457
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6148.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208148
_cod_database_fobs_code          2208148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.1480(3) 0.4585(2) 0.28037(17) 0.0347(5) Uani d . 1 N
H1 0.0502 0.4316 0.3179 0.042 Uiso calc R 1 H
C2 0.1944(3) 0.4382(2) 0.1837(2) 0.0323(5) Uani d . 1 C
C21 0.0738(4) 0.3675(3) 0.1457(3) 0.0478(7) Uani d . 1 C
H21A -0.0333 0.3549 0.1944 0.072 Uiso calc R 1 H
H21B 0.1296 0.2825 0.1477 0.072 Uiso calc R 1 H
H21C 0.0475 0.4198 0.0708 0.072 Uiso calc R 1 H
N3 0.3405(3) 0.47765(19) 0.12273(17) 0.0314(4) Uani d . 1 N
C4 0.4493(3) 0.5414(2) 0.1588(2) 0.0298(5) Uani d . 1 C
N41 0.5944(3) 0.5797(2) 0.09383(19) 0.0413(5) Uani d . 1 N
H41A 0.6160 0.5641 0.0324 0.050 Uiso calc R 1 H
H41B 0.6674 0.6204 0.1129 0.050 Uiso calc R 1 H
C5 0.4062(3) 0.5634(2) 0.2624(2) 0.0304(5) Uani d . 1 C
C6 0.2519(3) 0.5202(2) 0.3199(2) 0.0336(5) Uani d . 1 C
H6 0.2172 0.5333 0.3873 0.040 Uiso calc R 1 H
C7 0.5282(3) 0.6218(2) 0.3115(2) 0.0336(5) Uani d . 1 C
H7A 0.4933 0.5988 0.3909 0.040 Uiso calc R 1 H
H7B 0.6464 0.5816 0.3033 0.040 Uiso calc R 1 H
N8 0.5312(3) 0.76825(19) 0.25995(16) 0.0291(4) Uani d . 1 N
C9 0.6386(3) 0.8379(2) 0.2956(2) 0.0299(5) Uani d . 1 C
C91 0.7607(4) 0.7659(3) 0.3829(2) 0.0428(6) Uani d . 1 C
H91A 0.6949 0.7132 0.4497 0.064 Uiso calc R 1 H
H91B 0.8204 0.8291 0.3991 0.064 Uiso calc R 1 H
H91C 0.8454 0.7088 0.3564 0.064 Uiso calc R 1 H
C10 0.6183(3) 0.9702(2) 0.2391(2) 0.0332(5) Uani d . 1 C
S11 0.46545(10) 1.00560(7) 0.14321(6) 0.0433(2) Uani d . 1 S
C12 0.4324(3) 0.8441(3) 0.1807(2) 0.0361(6) Uani d . 1 C
H12 0.3536 0.8118 0.1493 0.043 Uiso calc R 1 H
C13 0.7135(4) 1.0794(3) 0.2476(3) 0.0409(6) Uani d . 1 C
H13A 0.8154 1.0949 0.1931 0.049 Uiso calc R 1 H
H13B 0.7555 1.0501 0.3212 0.049 Uiso calc R 1 H
C14 0.6021(4) 1.2085(3) 0.2288(3) 0.0459(7) Uani d . 1 C
H14A 0.6761 1.2771 0.2249 0.055 Uiso calc R 1 H
H14B 0.5530 1.2347 0.1576 0.055 Uiso calc R 1 H
O15 0.4637(3) 1.2002(2) 0.3137(2) 0.0598(6) Uani d . 1 O
H15 0.5077 1.2319 0.3554 0.116(18) Uiso d . 1 H
S1 0.99096(9) 0.79812(6) 0.07022(6) 0.03742(18) Uani d . 1 S
O11 1.0025(3) 0.8811(2) 0.14258(18) 0.0534(5) Uani d . 1 O
H11 1.0347 0.9545 0.1029 0.080 Uiso calc R 1 H
O12 1.1662(3) 0.7611(2) 0.0341(2) 0.0571(6) Uani d . 1 O
O13 0.8921(3) 0.8836(2) -0.02639(19) 0.0570(6) Uani d . 1 O
O14 0.8906(3) 0.6874(2) 0.13748(19) 0.0566(6) Uani d . 1 O
S2 1.20797(9) 0.71565(7) 0.53626(6) 0.03922(18) Uani d . 1 S
O21 1.1873(3) 0.8025(2) 0.41292(17) 0.0581(6) Uani d . 1 O
H21 1.1893 0.8812 0.4048 0.087 Uiso calc R 1 H
O22 1.1417(3) 0.5941(2) 0.55027(19) 0.0588(6) Uani d . 1 O
O23 1.3941(3) 0.6997(3) 0.5507(2) 0.0608(6) Uani d . 1 O
O24 1.1068(3) 0.7829(3) 0.6057(2) 0.0631(6) Uani d . 1 O
O1W 1.1846(5) 1.0472(3) 0.3800(4) 0.1186(16) Uani d . 1 O
H1W 1.099(8) 1.092(6) 0.403(5) 0.119(19) Uiso d . 1 H
H2W 1.278(9) 1.092(7) 0.367(6) 0.16(3) Uiso d . 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 121.1(2) y
C2 N1 H1 119.4 ?
C6 N1 H1 119.4 ?
N3 C2 N1 122.1(2) ?
N3 C2 C21 119.7(2) ?
N1 C2 C21 118.2(2) ?
C2 C21 H21A 109.5 ?
C2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C2 N3 C4 118.9(2) ?
N41 C4 N3 116.4(2) ?
N41 C4 C5 122.8(2) ?
N3 C4 C5 120.8(2) ?
C4 N41 H41A 120.0 ?
C4 N41 H41B 120.0 ?
H41A N41 H41B 120.0 ?
C6 C5 C4 116.5(2) ?
C6 C5 C7 120.1(2) ?
C4 C5 C7 123.2(2) ?
N1 C6 C5 120.5(2) ?
N1 C6 H6 119.7 ?
C5 C6 H6 119.7 ?
N8 C7 C5 114.1(2) ?
N8 C7 H7A 108.7 ?
C5 C7 H7A 108.7 ?
N8 C7 H7B 108.7 ?
C5 C7 H7B 108.7 ?
H7A C7 H7B 107.6 ?
C12 N8 C9 114.4(2) ?
C12 N8 C7 124.3(2) ?
C9 N8 C7 121.3(2) ?
C10 C9 N8 111.5(2) ?
C10 C9 C91 127.7(2) ?
N8 C9 C91 120.8(2) ?
C9 C91 H91A 109.5 ?
C9 C91 H91B 109.5 ?
H91A C91 H91B 109.5 ?
C9 C91 H91C 109.5 ?
H91A C91 H91C 109.5 ?
H91B C91 H91C 109.5 ?
C9 C10 C13 128.7(2) ?
C9 C10 S11 110.65(18) ?
C13 C10 S11 120.6(2) ?
C12 S11 C10 91.53(13) ?
N8 C12 S11 111.94(19) ?
N8 C12 H12 124.0 ?
S11 C12 H12 124.0 ?
C10 C13 C14 113.8(2) ?
C10 C13 H13A 108.8 ?
C14 C13 H13A 108.8 ?
C10 C13 H13B 108.8 ?
C14 C13 H13B 108.8 ?
H13A C13 H13B 107.7 ?
O15 C14 C13 112.9(3) ?
O15 C14 H14A 109.0 ?
C13 C14 H14A 109.0 ?
O15 C14 H14B 109.0 ?
C13 C14 H14B 109.0 ?
H14A C14 H14B 107.8 ?
C14 O15 H15 102.0 ?
O12 S1 O14 114.32(15) ?
O12 S1 O13 111.35(15) ?
O14 S1 O13 109.27(14) ?
O12 S1 O11 107.80(14) ?
O14 S1 O11 106.70(14) ?
O13 S1 O11 107.03(14) ?
S1 O11 H11 109.5 ?
O22 S2 O24 112.33(15) ?
O22 S2 O23 111.84(16) ?
O24 S2 O23 112.31(14) ?
O22 S2 O21 104.81(14) ?
O24 S2 O21 107.99(16) ?
O23 S2 O21 107.06(16) ?
S2 O21 H21 109.5 ?
H1W O1W H2W 107(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.339(3) y
N1 C6 1.348(3) y
N1 H1 0.8600 ?
C2 N3 1.306(3) ?
C2 C21 1.494(4) ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
N3 C4 1.362(3) ?
C4 N41 1.317(3) ?
C4 C5 1.429(4) ?
N41 H41A 0.8600 ?
N41 H41B 0.8600 ?
C5 C6 1.353(4) ?
C5 C7 1.502(3) ?
C6 H6 0.9300 ?
C7 N8 1.480(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
N8 C12 1.318(3) ?
N8 C9 1.396(3) ?
C9 C10 1.349(4) ?
C9 C91 1.489(4) ?
C91 H91A 0.9600 ?
C91 H91B 0.9600 ?
C91 H91C 0.9600 ?
C10 C13 1.503(3) ?
C10 S11 1.724(3) ?
S11 C12 1.675(3) ?
C12 H12 0.9300 ?
C13 C14 1.504(4) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 O15 1.411(4) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
O15 H15 0.8500 ?
S1 O12 1.428(2) ?
S1 O14 1.440(2) ?
S1 O13 1.492(2) ?
S1 O11 1.524(2) ?
O11 H11 0.8200 ?
S2 O22 1.407(3) ?
S2 O24 1.446(2) ?
S2 O23 1.448(2) ?
S2 O21 1.543(2) ?
O21 H21 0.8200 ?
O1W H1W 0.85(6) ?
O1W H2W 0.87(7) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O22 2_666 0.86 2.06 2.864(4) 155
N41 H41A N3 2_665 0.86 2.18 3.039(4) 178
N41 H41B O14 . 0.86 2.04 2.877(3) 164
O15 H15 O23 2_776 0.85 1.894 2.746(3) 179
O11 H11 O13 2_775 0.82 1.79 2.604(4) 176
O21 H21 O1W . 0.82 1.70 2.519(4) 176
O1W H1W O24 2_776 0.85(6) 1.94(6) 2.754(4) 158(5)
O1W H2W O15 1_655 0.87(7) 1.86(7) 2.722(4) 170(6)
C12 H12 O12 1_455 0.93 2.43 3.346(4) 169
C6 H6 O22 1_455 0.93 2.40 3.326(4) 173
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N3 -0.6(4) ?
C6 N1 C2 C21 179.2(2) ?
N1 C2 N3 C4 0.1(4) ?
C21 C2 N3 C4 -179.7(2) ?
C2 N3 C4 N41 -179.6(2) ?
C2 N3 C4 C5 0.9(3) ?
N41 C4 C5 C6 179.2(2) ?
N3 C4 C5 C6 -1.3(3) ?
N41 C4 C5 C7 -5.2(4) ?
N3 C4 C5 C7 174.3(2) ?
C2 N1 C6 C5 0.0(4) ?
C4 C5 C6 N1 0.8(4) ?
C7 C5 C6 N1 -174.9(2) ?
C6 C5 C7 N8 -105.8(3) ?
C4 C5 C7 N8 78.7(3) y
C5 C7 N8 C12 2.5(3) y
C5 C7 N8 C9 -179.6(2) ?
C12 N8 C9 C10 -0.6(3) ?
C7 N8 C9 C10 -178.7(2) ?
C12 N8 C9 C91 -178.7(2) ?
C7 N8 C9 C91 3.2(3) ?
N8 C9 C10 C13 -177.1(2) ?
C91 C9 C10 C13 0.8(5) ?
N8 C9 C10 S11 0.3(3) ?
C91 C9 C10 S11 178.2(2) ?
C9 C10 S11 C12 0.1(2) ?
C13 C10 S11 C12 177.7(2) ?
C9 N8 C12 S11 0.7(3) ?
C7 N8 C12 S11 178.72(18) ?
C10 S11 C12 N8 -0.4(2) ?
C9 C10 C13 C14 -146.9(3) ?
S11 C10 C13 C14 36.0(3) y
C10 C13 C14 O15 66.8(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126484
